Family Night is Awkward Night
by Anonymonimus
Summary: Bill doesn't understand that "dressing up" doesn't mean putting on a dress when he's invited to a Pines family supper at a fancy restaurant. SMUT WARNING


It was just another lazy day at the Mystery Shack. The shop was closed for the day and Mabel and Dipper laid on the sofa, their legs entangled together as they watched TV shows. Most of what they watched were exaggerated reality TV series with stupidly forced drama. They were currently making their way through a The Bachelor marathon and Dipper thought it was hopelessly dumb though he would be lying if he said he wasn't enraptured by what he was seeing. There was just something so captivating about watching people needlessly being mean to one another while trying to steal the heart of the bachelor of the season.

"I really hope Cassie gets booted off this episode." Mabel said. "I hate her."

"Right?" Dipper agreed, "She's literally the biggest bitch."

"I like Lisa," Mabel said just as the camera panned to the woman in question, "She's super cute and her son's so adorable."

"Yeah but Dean seems like the party hard kind of guy," Dipper said, "The type of person who's not ready to settle down and be a good example or a father to a kid."

As they continued talking about which girl would be the best match for the bachelor, Ford walked by, scribbling things down into a fourth journal he had begun writing about two years ago. He paused and made his way into the living room.

"What are you kids watching?" He asked, glancing at the TV.

"The Bachelor." The twins said simultaneously.

"They got rid of two candidates last episode." Mabel said as the commercial break began to play, "A first for the show too! Two of the contestants, Jo and Charlie, realized they were gay and in love with each other. It was really cute."

"I will never understand your generation's fascination with reality television." Ford sighed, "Wouldn't you prefer to play outside or something?"

"Are you really going to grill us for spending too much time indoors?" Dipper snorted, "You? The guy who never leaves the basement?"

"I was just outside moments ago!" Ford defended.

"For two seconds." Mabel called out, "Yeah, we noticed!"

"Honestly, Grunkle Stan spends more time outside than any of us," Dipper said, "but even then he just sits on the porch and drinks beer all day."

"It's a miracle his liver hasn't exploded yet." Ford agreed with a nod.

"Maybe we should all go out or something." Mabel suggested, "As a family."

"But where?" Dipper asked, "There's nowhere to really go in Gravity Falls."

Mabel thought it through for a moment. Her idea sparked upon hearing the commercial break finish and The Bachelor starting again. "I know!" She said with a wide smile on her face, "We can go to that fancy restaurant tonight! We never really eat out anyway, this can be a nice family evening!"

"You mean the restaurant owned by the Northwests?" Ford asked.

"Don't you need to book a reservation, like, a month before?" Dipper asked.

"Yeah but I can ask Pacifica to pull some strings." Mabel said with a proud grin, "I'll even ask her to join us."

If there was one thing Dipper didn't understand, was how Mabel liked Pacifica after the latter had been so mean to her when they were younger. He still hadn't forgiven her but then he supposed his sister might just have a bigger heart. Regardless, it was still baffling to see how close the two had become over the past seven years. They'd gone from rivals to closest friends. Mabel actually spent more time with Pacifica than she did with Candy and Grenda whenever they came to Gravity Falls during the summers.

"So we're going out tonight, then?" Ford sighed, "I better find two nice suits and tell Stan to clean up."

"Yay!" Mabel cheered and then turned to her brother excitedly, "Oh, Dipper! You should invite Bill too!"

Dipper and Ford froze. "That's a terrible idea." They said in unison.

"I'm glad we at least agree on that, Dipper." Ford said.

"Aww, come on, why?" Mabel whined.

"That's literally a recipe for chaos." Dipper stated, "He's going to light everyone wearing a stupid hat on fire, throw food around, and probably pour water in his eyes again."

"But he's family now!" Mabel argued.

"How?" Ford snorted.

"He's dating Dipper!" Mabel reminded, "Until they break up, he's family!"

"I'm not even sure if going out like that is Bill's thing…" Dipper tried.

The brunet thought he might be able to convince his sister to leave the blond demon behind however, the latter was as bad as Beatle Juice. He had said his name one too many times and, suddenly, Bill fell through a blue portal that opened on the ceiling. He hit the ground with a loud smack, earning sympathetic winces from everyone in the room.

"Ha ha, ow!" He laughed and peeled himself from the ground, "I heard my name! Why are we talking about me?"

"We're having a family night out." Mabel said with a bright smile, "We wanted to know if you wanted to tag along."

"Mabel!" Dipper and Ford hissed.

"Sure!" Bill agreed with a laugh and began levitating, "Where are we going?"

"A fancy restaurant owned by Pacifica Northwest's family." Dipper said seriously, "That means you need to behave yourself."

"I _always_ behave myself!" Bill retorted and Ford rolled his eyes.

"You're also going to need to dress up." Dipper added, "So go find yourself something nice and remember to pay with the _money_ you earned."

Tension abruptly fell upon them and Bill frowned at the insinuation and his cheeks flushed red. It was clear that Dipper touched a sore spot and it made him angry but the demon said nothing. They stared each other down for a moment before Bill began ascending to the portal still open above his head.

"Be back by seven!" Mabel said.

The demon grumbled something before disappearing into the blue hole that closed itself soon after. Dipper let out a heavy sigh and glared at the ground.

"That…got awkward." Ford sighed, "I'm going to leave you two to talk about it or something."

He scurried out of the room and made a b-line for the front porch to talk with Grunkle Stan. Mabel, on the other hand, turned her worried gaze to her brother. Dipper didn't really want to talk about it. He knew his comment was uncalled for but it was something he couldn't help. He didn't think Bill would cheat on him but it was something he wouldn't put past him. The demon _had_ paid for goods and services through sex in the past without a second care.

"You having couple troubles, Brobro?" Mabel asked gently, "Was that why you didn't want to invite Bill...?"

Dipper sighed and slapped his hands over his face in exasperation, "No…" he groaned, "That was just me being a dick…"

"You sure?" Mabel persisted.

"Yeah, don't worry," Dipper said, "I'll apologize to him when he comes back."

"Right, well, if you want to talk about it…" Mabel said and trailed off.

"I know, you're my go to gal." Dipper said and shoved Mabel playfully, "But there's nothing to talk about. I was just an asshole." He sighed and then added: "But I'm going to need you to help me find an outfit."

Mabel smiled brightly and immediately jumped off the sofa in agreement. She grabbed Dipper's arm and dragged him to his room, forgetting to turn off the television. For the next few hours, she had him try on different combinations of proper clothes while she made reservations for the restaurant and convinced Pacifica to join them. Then Mabel took the liberty of fixing Dipper's hair and hiding his signature hat so as to keep him from wearing it. And though he got mad, she refused to give it back to him.

By seven, the entire Pines family was ready to go. Ford had convinced Stan to make an effort when he dressed up and it worked. He still looked like a crook but more like one of the classy ones. Ford also wore a clean suit – it was a bit dated in its style but still nice and it suited him well. Mabel had pulled on one of her colourful ball gowns that looked atrocious on mannequins and in magazines but impossibly elegant and beautiful on her. It was a strange style only she could pull off. And though they were gathered in the living room, ready to go, Bill was still nowhere to be found.

"Punctuality isn't his forte, is it?" Ford hummed.

"He's usually on time." Dipper said, slightly perplexed.

"We're going to be late if he makes us wait any longer." Mabel said worriedly.

"Pfft. Not with Grunkle Stan's driving." Dipper smirked.

They awkwardly waited a moment longer but when ten minutes passed and Bill was nowhere to be found, they started to grow impatient. Mabel suggested they huddle in the car and start it while Dipper continued to wait in the house for Bill to show up. Dipper took a seat on the sofa and continued watching the marathon of The Bachelor while he waited. He hardly got the chance to get comfortable when a blue portal opened on the floor and spat Bill out.

"Ta-da!" The blond yelled proudly, his hands raised in the air like he had pulled a miraculous feat.

Dipper choked on his saliva when he caught sight of the demon. He wore a short, yellow, silk dress with a black belt over the waist and black high heels to match. Bill had even taken the time to apply makeup to his face and it looked immaculate – like a professional had done it for him. And as confused and irritated as Dipper was to see the blond had taken their invitation as a joke, he couldn't deny just how stunning he was. The feeling of appreciation went straight to his pants and, had they had more time on their hands, he would have taken Bill back to his bed for a bit of fun beneath the sheets.

"Bill!" Dipper snapped, "What the _hell_ are you wearing!?"

"A dress." Bill said and smiled happily as he glanced at his outfit.

Dipper gritted his teeth and shut his eyes. He counted to ten quickly in the hopes of relaxing before speaking again. "I know." He said stiffly, " _Why_?"

"What do you mean why?" The demon asked and he seemed genuinely confused. "You told me to dress up." He then looked Dipper over questionably, "Why aren't _you_ wearing a dress?"

Dipper pinched the bridge of his nose and forced himself to take in deep breaths. " _Bill_." He said evenly, "Getting 'dressed up' doesn't mean putting on a dress, it just means to put on some clothes."

Bill stared at him dumbly in a moment of silence. "But I _am_ wearing clothes." He pointed out.

"You're not supposed to be wearing a dress, you're supposed to be wearing a suit." Dipper nearly snapped.

"What if I _wanted_ to wear a dress?" Bill frowned.

Dipper took a step back for a moment. One of two things was happening: either Bill was joking or he was serious. Dipper had no problem with men or women wanting to cross-dress and if that was what the demon liked, then he wouldn't get mad at him over it. He was open-minded and ready to accept anyone with quirks, habits, or likes that deviated from the norm. The last thing he wanted Bill to think was that he was an unsupportive jerk – provided he really wasn't messing around. However, the brunet wasn't sure if Bill was still bitter about the comment he had made earlier and he had chosen the given way to lash back.

"Did you?" Dipper asked with an exasperated sigh. "Did you really or are you trying to be a smartass?"

Bill raised his eyebrows in surprise. "I wanted to." He said.

"You're serious?" The brunet asked.

"Yes…?" Bill answered, confused by the line of questioning.

"Then I'm sorry I was getting mad." Dipper apologized, "You look really cute in a dress."

Bill blushed and smiled widely, hovering a few inches higher. "You like what you see, hun?" he chuckled excitedly.

"Yeah, you did a good job." Dipper smiled, "I'm also sorry about the thing I said earlier, by the way."

"Eh, I'm over it." Bill shrugged, "I guess I understand where you're coming from."

Dipper smiled; a weight having been lifted off his shoulders. He was glad talking to Bill like he had was so easy. He had never been as smooth with previous boyfriends and girlfriends. The previous situation would have escalated into some sort of argument that would have been way out of proportion with any of them.

"So…" Bill then trailed off expectantly with a bright smile.

"So?" Dipper asked.

"Keep going! Tell me how you find me pretty!" Bill insisted, floating closer to his human.

Dipper rolled his eyes, "You're gorgeous but I think that even when you're just dressed casually." Dipper said and he couldn't resist the lecherous things that found their way into his head, "But like this…" he continued, looking Bill over with hungry eyes, "The things I want to do to you…"

The blush on Bill's face spread and he bit his lower lip as he hovered to the ground just as the portal closed beneath his feet. "Yeah…?" he said, his quiet voice dripping with lust.

Dipper's smirk quickly became libidinous. He took a step forward, invading the demon's personal space and bringing his lips inches away from the other's. "Mm-hm," he hummed lowly, "I'll show you when we get back from the restaurant…"

Bill's breath hitched. "I don't want to wait that long." He said and threw his arms around Dipper to pull him into a kiss.

Tongues rubbed against one another in a show for dominance – one that Dipper won. Bill abandoned himself to his control with great pleasure. He pulled them back onto the sofa, opening his legs to allow his human a more comfortable position as they continued to kiss with a furious passion. Their groins met with uncontrollable thrusts and cants of the hips, drawing breathy moans from both of their abused lips.

Dipper felt his pants rapidly become far too tight for any comfort just as his common sense was ready to fly out of his head. He broke the kiss he shared with Bill and the sight of the blond demon laying beneath him, looking utterly adorable in his yellow dress, his cheeks flushed red and his expression needy and lustful, was too arousing. The brunet was just about ready to make his family wait a tad longer if it meant he could make his lover scream his name to the heavens while fucking his brains out.

"Bill…" he said lowly, his voice heavy with lust. He shook his head and forced himself to look away, "We can't…not right now…"

"Sure we can…" Bill insisted, "Look—"

Bill took Dipper's hand and brought it between his legs. The latter held his breath and blushed deeply, even more so when his fingers slipped beneath the silk underclothes and probed the demon's entrance. However, he soon realized there was something unusual about it, like it was already stretched and lubricated seeing as he did feel a sort of thick wetness. Dipper's eyes went from between Bill's legs to his eyes and his grinning expression confirmed everything.

"You prepped yourself?" Dipper asked incredulously, "Just for me?"

"Yup!" Bill grinned, "Why did you think I took so long?'

"So you planed this?" Dipper smirked.

"Not exactly…" Bill admitted, "I just knew I'd turn you on and you'd turn me on but then you'd say something like "not right now, later" which I didn't want." He then lifted his legs to remove his underwear and throw them aside, "So we have time for a quickie, right?"

Dipper knew his family was still waiting impatiently inside the car and they had been for a while. A part of him didn't want to stall any longer but he knew his boner wasn't about to leave any time soon. He ultimately decided it was in his and his family's best interest if he just fucked the blond. It was the only way his erection would leave quickly and they would all be able to avoid any awkwardness. With that decided, Dipper pulled out his cock from its tight confines with a sigh of relief while Bill wiggled excitedly, spreading his legs further apart.

"The things you make me do…" Dipper whispered as he aligned himself.

"Enough chit chat, Pine Tree." Bill purred and slipped his arms around his neck to pull him down into a kiss.

Dipper then slowly pushed his dick into Bill, finding it went in rather smoothly and with little resistance. The demon really had done a good job of preparing himself – he was just as good as Dipper himself was when he took his time. Bill seemed to read his human's thoughts and grinned lazily, his features overcome with lust. They kissed again and the brunet began thrusting faster and harder. Bill's hands found their way to his hair, combing through them yet messing up the work Mabel had done earlier. Every now and then, he would grip at it tightly when Dipper would hit his prostate just the right way.

They had never been so close for so long while having sex before. There had always been a gap between their torsos mostly because Dipper enjoyed the sight of Bill as a moaning mess beneath him. But the way they fucked then was great in its own way. The brunet enjoyed catching the demon's moans and cries of ecstasy in his mouth as they continued to kiss, he loved how their breaths mingled when they would break apart for just a moment, and the scent of Bill was so strong from such a proximity, it overwhelmed his senses with lust. Everything made a sort of fog rise to Dipper's head – or rather his mind. To put it simply, everything about his lover, in that moment, gave him a high and increased the pleasure he felt tenfold.

It drove him insane in the most wonderful of ways.

The two were lost in each other. Their minds clogged with lust and their eyes solely resting on the other. They were so enraptured they failed to hear Grunkle Stan's car door creak open with a high pitched screech and close shut loudly. And as the steps of someone climbing the few stairs of the porch to the front door echoed outside, Bill began tightening around Dipper's erection, both feeling the beginnings of their climax. They came together, dirtying their clothes with warm semen, just as the front door opened. Neither had time to recover before freezing stiffly as Ford walked in and called:

"Dipper?"

Ford then walked into the living room finding them on the couch in a compromising position with evidence mounted against them. They darted their heads towards him, Dipper blushing something terrible while Bill just seemed offended. Ford, on the other hand, stood in the door way with a dumb expression, a gaping mouth, and a blush slowly creeping on his cheeks.

"I…" He tried but his voice trailed off.

The situation grew more awkward by the second. Dipper wished the ground would just swallow him and Bill. It would make the mortification end far sooner. He knew he should have resisted Bill more adamantly and he cursed his penis for having convinced him to be foolish.

"I'll go…" Ford mumbled dumbly.

He made way for the front door but ran right into the wall, stumbling and fumbling afterwards until the door opened and he felt the scene. Dipper smacked his hands in his face and groaned loudly, dropping his head on Bill's chest.

"Oh my god…" he whined. "This is so humiliating…"

"The nerve of that guy!" Bill huffed out – he was clearly on a different wave length.

"Bill, no." Dipper groaned, he pulled out of Bill and grabbed a couple of tissues on the small table next to the sofa to clean himself, "You don't understand how embarrassing this is for me…we probably scarred him…"

"Why?" Bill asked cluelessly. "Isn't what we did normal?"

"Yes, but—gah!" Dipper groaned, the urge to claw his face out steadily becoming overpowering. "It's not something you want the world to see! Least of all your great uncle!"

"Meh, I don't see the issue." Bill huffed, he snapped his fingers together and suddenly the semen was gone and he was completely clean.

"Of course you don't…" Dipper sighed dejectedly. "I don't suppose you can wipe that from his memories?"

"Nope, you came blame yourself for that." Bill said, "I don't think it would change much, he's probably already told Shooting Star and the old man."

Dipper stiffened and cringed further. "You really suck at making things better…" he mumbled.

"You're just being a baby!" Bill smirked and shoved Dipper playfully, "Now let's go! I'm getting hungry!"

Without warning, the demon teleported them into the vacant seats of the vehicle. It scared Mabel and Grunkle Stan but Ford was the one to scream like a little girl. The looks Mabel and Stan gave him suggested that Bill was wrong and Ford hadn't said anything but that family night was still the most awkward night Dipper ever had to endure.


End file.
